Claire was another girl who lived in Little Haven. Angela didn’t really know her; they had met a couple of times, but she wasn’t one of her friends. Claire was so shy and withdrawn, and while Angela didn’t know much about her as an age player, she could tell that she played at a particularly young age, especially compared to Angela and her friends. Her daddy and Charlie were planning to go out tonight and had decided that it would be fun for Angela to babysit Claire.
Angela sometimes did babysit the other girls in the community. It could be fun sometimes, especially in the summer when they could run around in the yard. Besides, she liked having some authority once in a while. She even sometimes fantasized about spanking the girls that she looked after herself, lifting the skirts of their babyish little dresses and pulling down their Barbie-doll panties before turning them over her lap for a good, hard punishment, but Charlie had made it clear long ago that this was forbidden. Especially with his threat hanging in the air, she didn’t want to take any risks, so she abandoned that train of thought.
Angela didn’t feel like chatting with Claire, so she started a conversation with Liz, a friend who lived in Texas. She had gotten to know her over an age play forum and had never actually met her in person, but she was a trusted confidante.
Angela typed, the words appearing on the screen in pink font on a baby blue background.
Hey, how are things?
Having custom fonts online had stopped being cool ages ago, but Angela clung to things that she remembered from her teenage years, or her ‘first teenage years’ as she liked to think of them.
Liz replied almost instantly.
Life is good. Staying out of trouble?
Angela quickly typed back.
Nah, never. I’m sitting on a sore bottom as we speak.
Angela began to tell Liz about everything which had happened last night, and Liz had asked lots of questions about the spanking Angela had received, although she got quite giggly when Angela started to talk about the sexy parts.
Right when they were getting to the best part of the story, another tab on the messaging program started to flash, signifying the start of a new conversation. It was with Charlie.
Shit, Angela thought before she even clicked on it to read it. I forgot to go on invisible.
The plain black font seemed to emphasize the sternness of Charlie’s words:
Angela, you know perfectly well that you are strictly forbidden from using messenger when you’re supposed to be working on applying for jobs. You can chat once your work is done, not during.
Sorrrrryyyyyy, daddy. I’ll sign out now and get back to work.
I think you need something to focus your mind on what you should be doing. I would have thought that a sore bottom would be enough, but it apparently isn’t. Let’s see if having something in your bottom hole does the trick.
Angela’s face grew ashen as she read the words and her heart rate sped up. Anal play was something that had been newly introduced, and Angela found it far too embarrassing to cope with. The feeling of her daddy spreading her cheeks and then inserting one lubed finger into her bottom hole made her face burn with humiliation, and the stretching feeling of fullness that the plug that followed caused was truly uncomfortable, at least at first.
The idea that she would have to insert the plug herself was mortifying. She wasn’t sure she could even do it. She squirmed in her seat uncomfortably, unsure of what to do.
Finally, she typed back, adding an emoticon in an attempt to signify her displeasure at the idea:
Yes, daddy >_<
Go upstairs and get your purple plug and the lube and then come back and wait for my instructions.
Angela considered disobeying, but she didn’t want to get caught not following through with a punishment, even though she wasn’t sure how he was going to find out whether or not she did what she was told. Still, her daddy could be tricky sometimes, and she knew it was best to just obey.
Yes, sir.
She typed ‘brb’ in her other conversation window and then headed upstairs.
In her bedroom, Angela opened the top drawer of Charlie’s dresser, where most of the toys were kept. The drawer was a strange mix of things. There were things that Angela loved and constantly desired to have used, like the fuzzy glove used to rub her bottom after a spanking and, of course, her vibrators. There were also plenty of things that made Angela’s body tighten with nervousness, like the butt plug that she had been sent for. She found it and the lubricant, and then shut the drawer and hurried downstairs.
I have them, daddy.
Good girl. Tell your friends that you’re chatting to that you’re going to have to go because you’re being punished for being a naughty girl and disobeying your daddy, and that you aren’t supposed to be online during the day.
With no one present to prevent her from doing so, Angela stomped her foot. She didn’t want to tell Liz that she was in trouble again. Liz could be even feistier than Angela, and she thought that she might get teased.
Angela typed a quick message to Liz:
Ugh. I have to go because I got in trouble by my daddy for being online during the day when I’m supposed to be applying for jobs.
Liz’s message came moments later:
Sucks to suck. You probably deserve it, always breaking all the rules.
Angela wrote back quickly, then closed the window:
You’re one to talk! Bye for now!
Then she typed to her daddy:
Ok, I told her.
Good. Now stand up and pull down your pants and panties.
Angela slowly stood up and did as she was told, butterflies growing in her stomach as she did.
Ok, I did.
Charlie’s message appeared in moments:
Now set the plug in front of you and think about where it’s going to go, and the fact that you’re going to put it there. If you can disobey me when I’m not around, you can be punished when I’m not, either.
Heat grew on Angela’s face as she set the purple butt plug on the table in front of her. Even if she hadn’t been instructed to think about it and contemplate what was going to happen next, she wouldn’t have been able to do anything else. It looked so big, the widest part seeming so flared to her, even though she knew it was one of the smaller plugs that was available at the store where they purchased it.
Once, when she had gone over to her friend Becca’s house on the other side of Little Haven, she had opened up their medicine cabinet in search of dental floss. There, she had seen a couple of Becca’s butt plugs, all lined up and waiting until they had to be used next. She had been so taken aback by seeing them, but also by how much bigger they were than the ones that Charlie had purchased for her. They still weren’t huge, but Angela found it somehow even more embarrassing to know that her friend could take a much bigger plug than she could. She didn’t like feeling inexperienced.
A message from Charlie showed up in the conversation window:
Have you been thinking about it?
Yes, daddy.
I’m glad. Now I want you to go get your phone. Text me when you have it.
Angela panicked a little bit. What was he going to do? Was he going to call her and walk her through putting the plug in, so he could hear her whimpers and sighs? He was at work, though. Surely he couldn’t do that.
Still, Angela went and found her phone, which was covered in a pale lilac case with white polka dots. She sat down on the chair at her computer desk and texted him that she was ready for whatever he wanted her to do next.
Within a few seconds, her phone vibrated again.
Get the phone stand.
Not sure why, Angela rummaged through her desk drawer until she found the small stand that she used to prop up her phone when she was using it to video-call someone. Then she texted Charlie, her thumb moving quickly across the screen.
Ok, I have it.
He wrote back a moment later:
Set your phone on it and put the camera on self-timer, then spread
your cheeks and take a photo of where that plug is going to go and send it to me.
Angela felt the butterflies in her stomach increasing, and looked around to see if anyone could see her out the window. No one was around, of course, but the snow was softly falling outside again, and that little motion gave her the feeling of being watched, so she got up and closed the blinds. She opened her phone’s camera and set it up like she had been told to, then, taking a deep breath to gather courage, she posed herself in front of it.
Charlie sometimes asked Angela to take naughty photos for him, especially when he had to go to a convention or when Angela was visiting her family in California. He also sometimes embarrassed her by ordering her into the pose she was about to adopt, with her cheeks spread and her most private area on full display. She had never been photographed this way before, though, and she had certainly never taken the picture herself.
It took another few seconds to build up the courage to set the self-timer and then get into the humiliating pose, grabbing her fleshy cheeks and pulling them to the sides. Even though no one was watching, her face burned as she stood there on display.
The worst part was when she had finished taking the picture and had to send it to her daddy, though: this meant that she had to look at it. Angela rarely ever saw herself when she was in such a humiliating position, and the image on the screen showed a part of her body that most people would never see. She had done a good job of spreading her cheeks apart, and her tight, puffy bottom hole was well displayed. Looking at it for just a moment made Angela want to cover her face with her hands, but she managed to send the snapshot to Charlie.
After a moment, he wrote back:
Well done. Now set it for a longer timer, lube up your finger, and warm yourself up. Make sure you get a good clear shot of your finger in your tight little hole.
Angela knew that her bottom hole needed to get used to being filled before it could fit the plug, but she hadn’t really thought about how that was going to happen. Her daddy always did this process for her, and it hadn’t ever occurred to her just how humiliating it was to have to finger her own bottom. She obviously masturbated, and not infrequently, but she had always left anal play up to her partner, and the change made it somehow feel more shameful to her.
Please, daddy, can’t you just do this when you get home?
No, darling. I told you before: if you disobey me when I’m not there to watch you, you can be punished that way, too.
Angela pouted for a moment, but accepted that her fate was inevitable. No matter how much it embarrassed her, she was going to have to take these photos for Charlie. She set the camera up with the timer waiting for a minute, then bent over the back of her chair. Just being in this position, with her bottom high and vulnerable and her legs apart made her blush, usually, and presenting herself to the camera made it really feel like a punishment.
As was always the case in these situations, Angela felt herself growing wet between her legs. She wished she could be slipping her finger into that hole instead of what she was about to do. Still, she grabbed the lubricant anyway, and applied a generous amount to her finger. Spreading her cheeks with her free hand, she rubbed a dab of it onto the outside of her hole, just like her daddy would have done if he was there. The lube always felt so cold, and the wet, slippery texture signaled to her what, exactly, was going to happen next. Then, taking a deep breath in first, she started to tease her finger against the tight entry.
“Relax,” she said aloud to herself, doing some deep breathing. She did, and she carefully worked her finger in. She began to work it back and forth, just like Charlie would have done to prepare her for the plug. The feeling was not unpleasant, and she felt herself growing more aroused as she did it, but when she heard the timer on the camera start to count down to the shutter, her muscles involuntarily tightened around her finger with shame.
Click, went the shutter. Angela continued to move her finger in her tight hole to loosen it up and get it ready for the plug, helping herself to relax by reaching her other hand around to stroke her clit while she did so. It was effective, and as she grew wetter and wetter, she was able to move the finger in her bottom hole more comfortably. It felt slick and glossy. She knew she was ready for the plug.
Angela slipped her finger out and quickly wiped her hands off with a paper towel from her desk before sending the photo to Charlie.
I’m ready for the plug, daddy.
Charlie’s response came moments later:
That’s a very good little girl. Put it all the way in and take a photo. You’ll wear it until I get home, and any time that I ask for one, you’ll send me another picture, understood?
Angela groaned at these instructions, but typed her agreement to them. As Charlie had probably figured out, Angela sometimes cheated at her punishments if she had any control over them, so by asking for photos like this he was guaranteeing that she was going to continue to have the uncomfortable little plug in her bottom until he returned.
Angela again set the camera up, then lubed the plug up well. As she stroked the soft surface of it, she thought nervously about how wide the biggest part was. She knew exactly how it felt as her bottom hole stretched to take it, and she shuddered a little.
Finally, she bent over and pressed the pointed end of the plug against her tight opening. With all the lube and preparation, it only took a moment for her to start sliding it in. The first bit went in easily, but as it began to flare out, Angela had to concentrate on relaxing. It was so much harder to push it in herself than to feel the helpless sensation of her daddy sliding the intruder up her little shaft. She managed to get closer to the biggest part, and, once again, in order to relax herself, began to stroke her clit.
Angela claimed that she hated the feeling of having the plug in, especially when it stretched like this and made her feel so full, but when she truly admitted it to herself, it made her incredibly aroused. She couldn’t wait until she had the plug fully inserted so she could masturbate properly.
As she pushed the plug further, she felt things start to feel particularly uncomfortable, but her arousal allowed her to keep going, letting it work its way further and further into her bottom. Finally, the stretching, full feeling reached its apex, and Angela let out a little yelp before her final push cleared the widest part, allowing her muscles to clamp down on the neck.
Feeling well stuffed with the plug, she carefully finished pushing it in, so that the base was pressed right against the outside of her anus. The base was a little bit wide, and it kept her cheeks just slightly apart. She knew, though, that the camera would start counting down soon, so after taking a second to catch her breath, she reached back and spread herself again, so that in the photo the full insertion of the butt plug would be visible. Doing this made her muscles twitch again, contracting against the neck and giving her another wave of arousal.
After the camera clicked its shutter, Angela got up. She found it hard to walk with the butt plug in; each motion made it slip and slide a little bit inside her, and made it very obvious that it was there. She gently shuffled across the room to the bathroom, where she washed the lube off her hands before she went back to send the final, disgraceful picture to her daddy.
Charlie was obviously pleased with her work, and reminded her that she was to leave the plug in her bottom no matter what she was doing for the rest of the day.
Angela knew that she was supposed to be getting back to work now, but the process of inserting this herself had made her so horny that she decided that she could get away with taking a couple of minutes of ‘alone time,’ as Charlie called it when she touched herself.
She lay back on the sofa, letting her weight press down on the plug. She felt it push itself back into position, having wiggled a bit when she was walking, and the fullness was delightful this time. Angela gently inserted one of her fingers into her very wet pussy, enjoying the feeling of having both of her holes filled at once.
She wondered how it would feel to be fu
cked while wearing the plug, the feeling of Charlie’s stiff cock on the other side of the silicone toy. She imagined this as she began to pull her fingers back and forth, swirling them around a bit to try to stimulate the feeling of the plug a bit.
The idea of her daddy fucking her while she wore the plug brought another idea into her head, one that both sparked passion and terrified Angela. She imagined how it would feel if Charlie was to fuck her in the ass. She thought about how he would go through the same process that she had just done, warming her little hole up for his cock, and how embarrassed she would feel knowing what was going to happen next. She thought about how it would feel as his hard member gently probed at her entrance, and then the slick, sudden, filling feeling of his insertion into her.
She imagined how helpless she would feel as he held her tightly in place to fuck her this way, every part of her body truly owned by him as he penetrated her, hard. She imagined how it would make her wail and cry out, how it would surely hurt, and how he wouldn’t stop, and would go hard and deep to really drive his point home: she belonged to him and he was totally and entirely entitled to her body.
She had begun to circle her clit with her fingers, going faster and faster as the thoughts of her fantasy got more and more clear. Suddenly, and a bit without warning, she found the perfect rhythm and felt her body grow warmer, her muscles tightening, blood rushing to her head, her face growing hot. Then orgasm ripped through her body, making her clench hard against the plug. This sudden reminder of its presence made her orgasm continue, blending into another, and then another as she wailed and cried on the sofa, her legs sticking straight out.
Daddy's Little Angela Page 3
